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<h1><a href="https://archiveofourown.org/works/27061894">F--- The Friend Zone</a> by <a class='authorlink' href='https://archiveofourown.org/users/Axelex12/pseuds/Axelex12'>Axelex12</a></h1>

<table class="full">

<tr><td><b>Category:</b></td><td>Original Work</td></tr>

<tr><td><b>Genre:</b></td><td>Age Difference, Bedroom Sex, Boss/Employee Relationship, Extramarital Affairs, F/M, First Time, Florida, Fluff and Angst, Fluff and Smut, Hotel Sex, Literal Sleeping Together, Loss of Virginity, MILFs, Multiple Orgasms, Multiple Sex Positions, Older Woman/Younger Man, Plot Twists, Porn With Plot, Porn with Feelings, Post-Coital Cuddling, Secret Relationship, Simultaneous Orgasm</td></tr>

<tr><td><b>Language:</b></td><td>English</td></tr>

<tr><td><b>Status:</b></td><td>Completed</td></tr>

<tr><td><b>Published:</b></td><td>2020-10-17</td></tr>

<tr><td><b>Updated:</b></td><td>2020-10-17</td></tr>

<tr><td><b>Packaged:</b></td><td>2021-05-06 21:27:34</td></tr>

<tr><td><b>Rating:</b></td><td>Explicit</td></tr>

<tr><td><b>Warnings:</b></td><td>Creator Chose Not To Use Archive Warnings</td></tr>

<tr><td><b>Chapters:</b></td><td>1</td></tr>

<tr><td><b>Words:</b></td><td>1,735</td></tr>

<tr><td><b>Publisher:</b></td><td>archiveofourown.org</td></tr>

<tr><td><b>Story URL:</b></td><td>https://archiveofourown.org/works/27061894</td></tr>

<tr><td><b>Author URL:</b></td><td>https://archiveofourown.org/users/Axelex12/pseuds/Axelex12</td></tr>

<tr><td><b>Summary:</b></td><td><div class="userstuff">
              <p>A Boss and her Secretary get it on in Miami.</p><p>Original work</p>
            </div></td></tr>

<tr><td><b>Relationships:</b></td><td>Original Female Character/Original Male Character</td></tr>

<tr><td><b>Comments:</b></td><td>3</td></tr>

<tr><td><b>Kudos:</b></td><td>7</td></tr>

</table>

<a name="section0001"><h2>F--- The Friend Zone</h2></a>
<div class="story"><div class="userstuff module">
    
    <p>It was a late night in her office and Rebecca was preparing to leave for the day. She and her assistant Leo had been staying late the night before they both headed off to a conference. Rebecca knew and had known for quite some time that Leo was head over heels in love with her. And if she was being honest she thought it was adorable and he was quite cute in an unconventional way. Rebecca got rather aroused at the notion that her young secretary was in love with her and she was not above teasing poor Leo if it gave her a chuckle. 
Now while Rebecca was married her husband was a bit of a serial cheater, her married life was anything but happy. Leo often gave her a very pleasant alternative with one slight difference. Leo never slept with her, he wanted to he desperately wanted to but he resisted his baser impulses. Rebecca had stopped into his office and to her surprise he had fallen asleep at his desk, she walked over to him and was prepared to wake him but she had a sexier idea in mind. She knelt down beside him and began to undo his belt, “I’ve bet you’ve been dreaming of this haven’t you sweetie?”<br/>
Leo was hung that much was clear, Rebecca had heard rumors from some of the women in the office. But to see him naked in person was something else entirely. Rebecca not one to miss a good photo opt pulled out her phone and took a photo of it just to capture the right moment. She spat in her hand and then began to genteelly stroke his dick making she got him nice and wet then a sensation spread across her thighs. “Oh God I’m defiantly getting on this while we’re gone maybe even some when we come back.” Rebecca placed her hand under Leo’s balls and let out a deep sigh as she marveled at how heavy his balls felt. Leo let out a grunt that surprised his boss, “Merde, till next time Mona mi.” 
She quickly got him dressed and evened out her clothes. “Oh hey Rebecca I’ll be done here in a minute.” She went to go and give him a peck on his cheek but as he turned their lips met. “Well Don’t be too long remember we have a plane to catch in the morning.” Leo smiled, “Yeah tonight New York tomorrow Miami.”<br/>

The next morning, they met at the airport waiting to board their jet Leo looked somewhat stressed out he had barley slept he was worried about this trip. As they boarded the jet he and Rebecca ended up sitting next to each other he thought about telling her about this weird sexual dream he had last night but he chose against it. 
“So are you excited to get away from the city for a few days?”, she asked him, clearly noticing he was nervous. 
Leo: “Yeah I’ve just never been this close to you before.”
Leo realized what he just said and made an attempt to clear up what he said but Rebecca patted his hand reassuringly and said, “It’s alright Leo I know what you mean by the way what’s our sleeping arrangements for this evening?” 
Leo pulled out his itinerary, “The hotel wasn’t able to give us the executive suite so they gave us the honeymoon one instead I can give you the bed and I’ll sleep on the couch if you like. Through some of my discounts I got the place fifty percent cheaper and also awarded us a complementary breakfast.”<br/>
Rebecca smiled one of the reasons she hired him he was always trying to anticipate her need. “How about car rental? Where are we on that?” 
Leo pulled out the car rental paper work: “we have a black Lincoln SRX, as requested.” 
Rebecca gave him a peck on the cheek approvingly making him somewhat blush. “So I have to ask since we will be gone for the holiday what do you normally do on Valentines day?”, Rebecca said.
Leo chuckled, “Well since I’m privileged not to have a girlfriend I stay home.” Rebecca smiled and placed her hand on his knee “You may be single but that doesn’t mean you’re not in love. So come on buddy tell your dear old boss who do you have the hot’s for?”<br/>
Leo was trying to keep his cool He knew Rebecca had some interesting ways of making people give her information but blatant seduction was not something he saw her use often. “what do I get out of telling you who I’m in love with, I’m pretty sure you know who it is anyway.” 
Rebecca moved her hand closer to his groin she could feel his dick getting hard and that in turn made her wet. “Let’s just say our vacation will be more interesting.” 
Leo looked back at her and relented, “She’s married besides I doubt she would even look at me as lover material.” 
Rebecca looked at him again her hungry eyes turning more compassionate. “Every time I see her I want to tell her that she’s amazing and that even though I’m just a secretary I want to try and make her as happy as possible.” 
Rebecca took his face in her hands and said “What if I told you that she sees how hard you try and that she knows that just by your actions how much you care for her and that your efforts have never gone unnoticed.” At this point the guessing game was over and right as Leo was going in for a kiss the voice came on the loud speaker. 
“Ladies and gentlemen welcome to Miami international airport we hope you enjoyed your flight with us.”<br/>
The walk to the car rental was quiet filled with things they each needed to say to each other, The drive out to the hotel wasn’t much better by the time they got to the hotel room you would think a large wall had come between them. “So I wasn’t sure if you wanted to head to the dinner or did you want to stay in?”, he asked.
Rebecca looked at him for a good long moment and then kissed him suddenly and deeply her tongue wrestling his she was a good two feet taller than him so she easily took him down on the bed. “Right now all I want is you we can worry about dinner later.<br/>
She removed his shirt, then his pants shoes and socks. Rebecca wanted him butt naked for what was coming next. She fell on her knees taking his large black dick into her hand. Rebecca rubbed and jerked Leo’s dick up and down. She noticed the reaction Leo and it made her giggle, “What’s wrong never had a woman jerk your cock?”<br/>
Leo looked at her and said simply, “No I’m a virgin.” Rebecca stopped and stared at him, “You’re a virgin?!?Seriously, you’ve never had sex?” 
Leo shook his head almost shamefully, “It wasn’t for a lack of trying but no I guess I was just waiting for the right woman. That doesn’t turn you off does it? Rebecca took his chin between her thumb and forefinger and smiled kissing his lips gently “No my love in fact it rather turns me on. The fact that you’ve been waiting on me to pop your cherry.” Rebecca propped Leo up in a more comfortable position on the bed then with out much hesitation. Put her mouth around the head of his dick. Leo found himself lasting much longer then he thought he would even though it was just a blow job.<br/>
Rebecca looked at him with a deep hunger she kissed him again and then got ready to mount him. She was surprised how large and thick he was she let out a slight moan of pain as she took him in. “I’m sorry I don’t mean to hurt you.” , he apologized.
She smiled “Think nothing of it love you’re just bigger than I thought, not to mention thicker too.”<br/>
Soon she started to fuck him she found it hard to try not to cry out in pleasure. 
Here she was with her personal assistant, her secretary her friend and she was about to get the best fuck of her life from him. She found herself on her back now, she was starring up at him her young lover. She noticed that he had a look of hopeful determination on his face, then she felt it the budding feeling of an orgasm. 
“Oh my God he’s going to make me cum!” 
On top of the budding orgasm Leo was leaving little love marks on her neck which only pleased Rebecca further. With each thrust of his dick Rebecca felt herself get closer and closer to coming.<br/>
She looked into his dark brown eyes her arm wrapping around his neck her legs wrapping around his waist.
“Oui!” She cried out as her lover made her come she scratched his chest as the typhoon of sexual pleasure crashed own on her. Rebecca basked in the afterglow of her orgasm and looked at Leo he hadn’t come yet and not wanting to come off as a selfish lover She pushed him down onto his back and got ready to fuck his brains out. “Now are you ready to have the best fuck of your life?”, Rebecca said.
Leo looked slightly scared but nodded as his boss looked down at him.<br/>
When it was over Rebecca looked at the man she freshly deflowered she laughed at the giddy grin he was trying to suppress. 
“So how did I do?”, she asked him he looked and his grin broke free and he replied, “You were great and that was amazing! Can we do it again?” 
Rebecca laughed and gave him a kiss. “Later lover boy how about you and me order us some dinner and then we’ll take a nice long hot bath and afterwards then we do this again okay?”, she asked.
Leo nodded and headed towards the bathroom to run Rebecca a bath. The Evening consisted mostly of eating and fucking. When they had fallen asleep Leo had cuddled up next to his boss his face resting on her breast Rebecca looked down at him and smiled, “Good night my sweet lover boy."</p>
  </div><div class="fff_chapter_notes fff_foot_notes"><b>Author's Note:</b><blockquote class="userstuff"><p>Leave kudos.</p></blockquote></div></div>
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